2-Naphthylamine → N-(2-naphthyl)alanine Ethyl Ester

HRID 860332Notes

Reaction equation

HRID 860332 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12]([O:17][CH2:18][CH3:19])(=[O:16])[C:13]([CH3:15])=O>>[CH2:18]([O:17][C:12](=[O:16])[C@H:13]([CH3:15])[NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)[CH3:19]

Participants

3

Reactant 2

HCID 70572-NaphthylamineHCID 12041Ethyl pyruvate

Product 1

HCID 11345542N-(2-naphthyl)alanine Ethyl Ester

Procedure

Following reductive amination General Procedure AA above and using 2-aminonaphthalene (Aldrich) and ethyl pyruvate (Aldrich), the title compound was prepared as a solid having a melting point of 52–56° C. The reaction was monitored by silica gel tlc (Rf=0.50 in 25% EtOAc/hexanes). Purification was by flash chromatography with silica gel using 25% EtOAc/hexanes as the eluant.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-747cf5b0558b48b086a8aa0f0a9ee0fb
Source dataset
uspto-grants-2006_12
Patent number
US07153847B2

Reaction notes

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